NPASS Compound

Structure

NPC281516 OpenBabel07101718232D 24 26 0 0 1 0 0 0 0 0999 V2000 4.3018 2.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0907 -3.6084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7168 0.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3979 1.2630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0055 1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9447 2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6370 1.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0550 0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9447 -2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2523 1.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8839 -1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2523 -1.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8839 1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6032 -2.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0055 -1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0550 -0.4817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8343 -0.4817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6216 -2.9657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6370 -1.3496 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8343 0.4817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9942 -0.6960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8359 -3.9049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4640 -2.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 2 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 9 1 1 0 0 0 16 19 1 6 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 3 1 1 0 0 0 19 24 1 0 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	3.576
LogD:	2.871
LogS:	-3.939
# Rotatable Bonds:	0
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	5.697
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	3.069786907872185e-05
Pgp-inhibitor:	0.859
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.322

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	91.6363296508789%
Volume Distribution (VD):	1.035
Pgp-substrate:	5.2167277336120605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.407
CYP2C9-inhibitor:	0.251
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.526
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	9.598
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.954
Carcinogencity:	0.435
Eye Corrosion:	0.719
Eye Irritation:	0.552
Respiratory Toxicity:	0.971

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC281516

Natural Product ID:	NPC281516
*Common Name:**	Sinulariolide
IUPAC Name:	n.a.
Synonyms:	Sinulariolide
Standard InCHIKey:	FONRUOAYELOHDC-ZOOQSLMQSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13-6-5-10-20(4)17(23-20)12-15-9-11-19(3,16(21)8-7-13)24-18(22)14(15)2/h6,15-17,21H,2,5,7-12H2,1,3-4H3/b13-6+/t15-,16+,17+,19-,20+/m1/s1
SMILES:	C/C/1=CCC[C@@]2(C)[C@H](C[C@H]3CC[C@](C)([C@H](CC1)O)OC(=O)C3=C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486377
PubChem CID:	15699347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087604]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	chinese soft coral	n.a.	PMID[18553926]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155971]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964704]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30528697]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644083]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2
IC50	7
Others	5

Activity Type	# Activity
Cell Line	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	8.5	ug ml-1	PMID[473260]
NPT137	Cell Line	L1210	Mus musculus	ED50	=	10.0	ug ml-1	PMID[473260]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4700.0	nM	PMID[473261]
NPT113	Cell Line	RAW264.7	Mus musculus	CC50	>	50000.0	nM	PMID[473261]
NPT113	Cell Line	RAW264.7	Mus musculus	Ratio CC50/IC50	>	10.6	n.a.	PMID[473261]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[473261]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	33600.0	nM	PMID[473261]
NPT4783	Cell Line	SNU-398	Homo sapiens	IC50	=	24700.0	nM	PMID[473261]
NPT2309	Cell Line	CAPAN-1	Homo sapiens	IC50	=	26100.0	nM	PMID[473261]
NPT4137	Cell Line	Splenocytes	Mus musculus	CC50	=	32300.0	nM	PMID[473262]
NPT4137	Cell Line	Splenocytes	Mus musculus	IC50	=	19500.0	nM	PMID[473262]
NPT4137	Cell Line	Splenocytes	Mus musculus	IC50	=	9200.0	nM	PMID[473262]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.6	n.a.	PMID[473262]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	3.5	n.a.	PMID[473262]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC281516 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1524
0.2-0.3	5400
0.3-0.4	12066
0.4-0.5	12545
0.5-0.6	7284
0.6-0.7	3052
0.7-0.8	522
0.8-0.85	53
0.85-0.9	13
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC248602
0.9524	High Similarity	NPC153805
0.9294	High Similarity	NPC227379
0.9294	High Similarity	NPC474471
0.9157	High Similarity	NPC11620
0.9091	High Similarity	NPC212486
0.9048	High Similarity	NPC72464
0.8989	High Similarity	NPC81386
0.8989	High Similarity	NPC474035
0.8941	High Similarity	NPC137033
0.8941	High Similarity	NPC329749
0.8889	High Similarity	NPC14961
0.8889	High Similarity	NPC270013
0.8864	High Similarity	NPC474761
0.8864	High Similarity	NPC476004
0.8851	High Similarity	NPC202672
0.8837	High Similarity	NPC474949
0.8837	High Similarity	NPC475019
0.8824	High Similarity	NPC9868
0.8764	High Similarity	NPC12172
0.8764	High Similarity	NPC184463
0.8764	High Similarity	NPC30515
0.8764	High Similarity	NPC208886
0.875	High Similarity	NPC307411
0.8721	High Similarity	NPC47958
0.8721	High Similarity	NPC149725
0.8721	High Similarity	NPC304509
0.8667	High Similarity	NPC475912
0.8667	High Similarity	NPC81419
0.8667	High Similarity	NPC179746
0.8652	High Similarity	NPC51004
0.8621	High Similarity	NPC122502
0.8621	High Similarity	NPC164393
0.8621	High Similarity	NPC476015
0.8621	High Similarity	NPC474762
0.8605	High Similarity	NPC474780
0.8605	High Similarity	NPC243618
0.8605	High Similarity	NPC70424
0.8588	High Similarity	NPC474291
0.8587	High Similarity	NPC476315
0.8571	High Similarity	NPC233377
0.8539	High Similarity	NPC173926
0.8523	High Similarity	NPC474765
0.8523	High Similarity	NPC231889
0.8488	Intermediate Similarity	NPC257358
0.8488	Intermediate Similarity	NPC474472
0.8478	Intermediate Similarity	NPC36954
0.8462	Intermediate Similarity	NPC476300
0.8421	Intermediate Similarity	NPC476270
0.8404	Intermediate Similarity	NPC473326
0.8387	Intermediate Similarity	NPC473859
0.837	Intermediate Similarity	NPC57405
0.837	Intermediate Similarity	NPC303942
0.837	Intermediate Similarity	NPC71589
0.8353	Intermediate Similarity	NPC474981
0.8352	Intermediate Similarity	NPC329952
0.8333	Intermediate Similarity	NPC151770
0.8333	Intermediate Similarity	NPC474032
0.8333	Intermediate Similarity	NPC474951
0.8316	Intermediate Similarity	NPC475053
0.8316	Intermediate Similarity	NPC288876
0.8315	Intermediate Similarity	NPC186148
0.8295	Intermediate Similarity	NPC21469
0.8295	Intermediate Similarity	NPC197903
0.8295	Intermediate Similarity	NPC474547
0.8295	Intermediate Similarity	NPC99395
0.828	Intermediate Similarity	NPC107476
0.828	Intermediate Similarity	NPC475659
0.8276	Intermediate Similarity	NPC170377
0.8276	Intermediate Similarity	NPC272814
0.8265	Intermediate Similarity	NPC243998
0.8242	Intermediate Similarity	NPC475748
0.8222	Intermediate Similarity	NPC58219
0.8222	Intermediate Similarity	NPC177629
0.8211	Intermediate Similarity	NPC474213
0.8202	Intermediate Similarity	NPC470242
0.8191	Intermediate Similarity	NPC279621
0.8182	Intermediate Similarity	NPC475963
0.8182	Intermediate Similarity	NPC3464
0.8182	Intermediate Similarity	NPC474776
0.8182	Intermediate Similarity	NPC151176
0.8163	Intermediate Similarity	NPC474741
0.8152	Intermediate Similarity	NPC475881
0.8152	Intermediate Similarity	NPC470379
0.8152	Intermediate Similarity	NPC70251
0.8152	Intermediate Similarity	NPC470373
0.8144	Intermediate Similarity	NPC474747
0.814	Intermediate Similarity	NPC103634
0.814	Intermediate Similarity	NPC474510
0.8132	Intermediate Similarity	NPC295312
0.8132	Intermediate Similarity	NPC92974
0.8111	Intermediate Similarity	NPC475703
0.8105	Intermediate Similarity	NPC40812
0.809	Intermediate Similarity	NPC50362
0.809	Intermediate Similarity	NPC319795
0.809	Intermediate Similarity	NPC38468
0.8085	Intermediate Similarity	NPC272050
0.8081	Intermediate Similarity	NPC223450
0.8068	Intermediate Similarity	NPC231601
0.8065	Intermediate Similarity	NPC475838
0.8065	Intermediate Similarity	NPC228451
0.8065	Intermediate Similarity	NPC125674
0.8061	Intermediate Similarity	NPC475945
0.8061	Intermediate Similarity	NPC475871
0.8043	Intermediate Similarity	NPC473448
0.8043	Intermediate Similarity	NPC473619
0.8041	Intermediate Similarity	NPC473332
0.8041	Intermediate Similarity	NPC474742
0.8022	Intermediate Similarity	NPC476704
0.8021	Intermediate Similarity	NPC83895
0.8021	Intermediate Similarity	NPC187761
0.8	Intermediate Similarity	NPC477513
0.798	Intermediate Similarity	NPC100487
0.7979	Intermediate Similarity	NPC473316
0.7979	Intermediate Similarity	NPC474247
0.7979	Intermediate Similarity	NPC473330
0.7959	Intermediate Similarity	NPC471148
0.7959	Intermediate Similarity	NPC225353
0.7957	Intermediate Similarity	NPC475972
0.7957	Intermediate Similarity	NPC473321
0.7938	Intermediate Similarity	NPC475949
0.7935	Intermediate Similarity	NPC166919
0.7935	Intermediate Similarity	NPC473564
0.7912	Intermediate Similarity	NPC5130
0.7912	Intermediate Similarity	NPC190753
0.79	Intermediate Similarity	NPC54737
0.7895	Intermediate Similarity	NPC471141
0.7889	Intermediate Similarity	NPC477018
0.7889	Intermediate Similarity	NPC100921
0.7879	Intermediate Similarity	NPC110989
0.7879	Intermediate Similarity	NPC475873
0.7872	Intermediate Similarity	NPC295204
0.7872	Intermediate Similarity	NPC273579
0.7872	Intermediate Similarity	NPC288240
0.7872	Intermediate Similarity	NPC162205
0.7872	Intermediate Similarity	NPC476049
0.7865	Intermediate Similarity	NPC250315
0.7857	Intermediate Similarity	NPC47880
0.7857	Intermediate Similarity	NPC201718
0.7857	Intermediate Similarity	NPC474339
0.7857	Intermediate Similarity	NPC164598
0.7849	Intermediate Similarity	NPC49342
0.7849	Intermediate Similarity	NPC469718
0.7849	Intermediate Similarity	NPC62815
0.7849	Intermediate Similarity	NPC251385
0.7849	Intermediate Similarity	NPC329857
0.7835	Intermediate Similarity	NPC308567
0.7835	Intermediate Similarity	NPC187268
0.7835	Intermediate Similarity	NPC222303
0.7835	Intermediate Similarity	NPC261377
0.7835	Intermediate Similarity	NPC255592
0.7835	Intermediate Similarity	NPC161855
0.7835	Intermediate Similarity	NPC471144
0.7826	Intermediate Similarity	NPC473715
0.7816	Intermediate Similarity	NPC470244
0.7816	Intermediate Similarity	NPC470239
0.7812	Intermediate Similarity	NPC230800
0.7812	Intermediate Similarity	NPC473291
0.7812	Intermediate Similarity	NPC476009
0.7802	Intermediate Similarity	NPC477010
0.7802	Intermediate Similarity	NPC309211
0.7802	Intermediate Similarity	NPC50637
0.7802	Intermediate Similarity	NPC284902
0.7802	Intermediate Similarity	NPC469676
0.78	Intermediate Similarity	NPC203659
0.7791	Intermediate Similarity	NPC84360
0.7789	Intermediate Similarity	NPC190294
0.7789	Intermediate Similarity	NPC471147
0.7778	Intermediate Similarity	NPC472957
0.7778	Intermediate Similarity	NPC149371
0.7778	Intermediate Similarity	NPC472958
0.7778	Intermediate Similarity	NPC86077
0.7766	Intermediate Similarity	NPC20713
0.7766	Intermediate Similarity	NPC131209
0.7766	Intermediate Similarity	NPC133698
0.7755	Intermediate Similarity	NPC186861
0.7755	Intermediate Similarity	NPC471381
0.7742	Intermediate Similarity	NPC83423
0.7732	Intermediate Similarity	NPC471150
0.7717	Intermediate Similarity	NPC473649
0.7717	Intermediate Similarity	NPC154097
0.7717	Intermediate Similarity	NPC179659
0.7717	Intermediate Similarity	NPC159750
0.7717	Intermediate Similarity	NPC470401
0.7717	Intermediate Similarity	NPC160138
0.7708	Intermediate Similarity	NPC474947
0.7708	Intermediate Similarity	NPC304886
0.7708	Intermediate Similarity	NPC475900
0.7708	Intermediate Similarity	NPC471142
0.77	Intermediate Similarity	NPC472755
0.7692	Intermediate Similarity	NPC261380
0.7684	Intermediate Similarity	NPC135776
0.7677	Intermediate Similarity	NPC472753
0.7677	Intermediate Similarity	NPC150923
0.767	Intermediate Similarity	NPC139838
0.767	Intermediate Similarity	NPC59489
0.7667	Intermediate Similarity	NPC53867
0.7667	Intermediate Similarity	NPC475842
0.766	Intermediate Similarity	NPC312042
0.766	Intermediate Similarity	NPC313670

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC281516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2215
0.2-0.3	3732
0.3-0.4	2007
0.4-0.5	671
0.5-0.6	250
0.6-0.7	32
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD46	Approved
0.8242	Intermediate Similarity	NPD6698	Approved
0.809	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7838	Discovery
0.7579	Intermediate Similarity	NPD7983	Approved
0.7429	Intermediate Similarity	NPD6371	Approved
0.7368	Intermediate Similarity	NPD1695	Approved
0.7308	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5344	Discontinued
0.7075	Intermediate Similarity	NPD6686	Approved
0.6972	Remote Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6435	Approved
0.6737	Remote Similarity	NPD7154	Phase 3
0.6731	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4632	Approved
0.6602	Remote Similarity	NPD7839	Suspended
0.66	Remote Similarity	NPD5785	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6535	Remote Similarity	NPD6411	Approved
0.6531	Remote Similarity	NPD5786	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6525	Remote Similarity	NPD7830	Approved
0.6525	Remote Similarity	NPD7829	Approved
0.6525	Remote Similarity	NPD7642	Approved
0.6486	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7507	Approved
0.6417	Remote Similarity	NPD8273	Phase 1
0.641	Remote Similarity	NPD6319	Approved
0.6395	Remote Similarity	NPD3197	Phase 1
0.6392	Remote Similarity	NPD6110	Phase 1
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4249	Approved
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8513	Phase 3
0.6356	Remote Similarity	NPD8516	Approved
0.6322	Remote Similarity	NPD7341	Phase 2
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6289	Remote Similarity	NPD5209	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.6263	Remote Similarity	NPD1694	Approved
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4819	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6239	Remote Similarity	NPD7641	Discontinued
0.6237	Remote Similarity	NPD8039	Approved
0.6228	Remote Similarity	NPD8297	Approved
0.6218	Remote Similarity	NPD5983	Phase 2
0.6216	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7909	Approved
0.62	Remote Similarity	NPD6422	Discontinued
0.618	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6148	Remote Similarity	NPD8451	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6098	Remote Similarity	NPD8448	Approved
0.6098	Remote Similarity	NPD8074	Phase 3
0.6095	Remote Similarity	NPD7748	Approved
0.6083	Remote Similarity	NPD8444	Approved
0.6082	Remote Similarity	NPD4252	Approved
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD5701	Approved
0.6066	Remote Similarity	NPD7492	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD7515	Phase 2
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.6038	Remote Similarity	NPD5695	Phase 3
0.6034	Remote Similarity	NPD8133	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6018	Remote Similarity	NPD7320	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5984	Remote Similarity	NPD8328	Phase 3
0.598	Remote Similarity	NPD7524	Approved
0.598	Remote Similarity	NPD3573	Approved
0.5968	Remote Similarity	NPD7078	Approved
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD6372	Approved
0.596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8390	Approved
0.5952	Remote Similarity	NPD8392	Approved
0.5952	Remote Similarity	NPD8391	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5938	Remote Similarity	NPD4756	Discovery
0.5935	Remote Similarity	NPD8342	Approved
0.5935	Remote Similarity	NPD8341	Approved
0.5935	Remote Similarity	NPD8340	Approved
0.5935	Remote Similarity	NPD8299	Approved
0.5926	Remote Similarity	NPD7902	Approved
0.592	Remote Similarity	NPD7736	Approved
0.5913	Remote Similarity	NPD6421	Discontinued
0.5913	Remote Similarity	NPD4634	Approved
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD6079	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5902	Remote Similarity	NPD5988	Approved
0.5902	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6684	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5872	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD6059	Approved
0.5865	Remote Similarity	NPD5328	Approved
0.5862	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5211	Phase 2
0.5842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3666	Approved
0.5842	Remote Similarity	NPD3665	Phase 1
0.5842	Remote Similarity	NPD3133	Approved
0.584	Remote Similarity	NPD8293	Discontinued
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	Approved
0.5833	Remote Similarity	NPD5221	Approved
0.5826	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD7503	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.581	Remote Similarity	NPD3168	Discontinued
0.58	Remote Similarity	NPD3667	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD7516	Approved
0.5783	Remote Similarity	NPD3172	Approved
0.578	Remote Similarity	NPD4755	Approved
0.578	Remote Similarity	NPD5173	Approved
0.5772	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD5737	Approved
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6903	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.5758	Remote Similarity	NPD4695	Discontinued
0.5752	Remote Similarity	NPD5141	Approved
0.575	Remote Similarity	NPD6317	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data